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38 Old Turnpike Road

Litchfield, Connecticut 06750

ACTIVE$1,100,000

Reduced from $1,495,000

Beds
3
Baths
2 | 1
SqFt
2,377
Acres
4.53
Year Built
1777
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

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Waterfront2-Car Garage3 FireplacesVirtual TourPrice Reduced

About This Home

An exceptional property with a rare convergence of historic provenance and modern excellence. This magical setting comprises a c.1777 home (once a Tollhouse), that blends 18th c. character, masterfully rebuilt in 2023. Step inside to a main floor that includes, a Kitchen, Dining Room, Parlor, Living Room & Primary BR suite including 3 FP's and a 3-season Solarium/Mudroom, Laundry room (ne' Buttery) and 1/2 BA. The Upper level has 2BR's and full bath. There are warm pine wood floors throughout. The enchanting park like setting includes, 3 parcels= 4.5ac.+-, with a pond, babbling stream, a 2-car barn-style garage with a ~400sf upper level studio incl. a sitting and sleeping area, a heated in-ground pool, well-established perennial gardens and pathways, stone walls and a gently rolling hill that borders the Land Trust. It is Connecticut pastoral perfection at its finest. WAIT!!! There's more...An opportunity to start a new, on-site business, currently, a 400 sf Antique Shop. For the collector, artisan or entrepreneur, seeking a life-work retreat or just pure tranquility. This is a one-of-a-kind property with incredible flexibility, delivering, history, beauty & endless possibilities, it is an extremely RARE opportunity. Are you ready to live your next chapter! Set between the storied villages of Litchfield, Bantam, New Preston & Washington for shopping, dining, hiking, skiing, boating or just relaxing. Conveniently located near top-tier area independent schools

Key Facts

City/Town
Litchfield
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1777
Days on Market
265 days
Beds
3
Baths
2 full · 1 half
Living Area
2,377 sq ft
Lot Size
4.53 acres
Garage / Parking
2 garage · 5 total
Property Taxes
$8,211 / Annually

Market Snapshot

The Litchfield Market

Single Family · trailing 12 months

Median Days on Market

83

19 active listings

Median $ / Sq Ft

$376

19 active listings

Sale-to-List Ratio

100.0%

74 sales

How this home compares

List Price

$1.10M

vs $895,000 median

22.9% above median

Price / Sq Ft

$463

vs $376 median

23.1% above median

Days on Market

265 days

vs 83 days median

182 days longer than median

Based on 19 active and 74 closed sales (trailing 12 mo) of single family in Litchfield. Source: SmartMLS · As of July 28, 2026.

Location

38 Old Turnpike Road, Litchfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,660

per month

  • Principal & Interest$5,609
  • Property Taxes$684
  • Insurance$367
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Litchfield
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1777
New Construction
No/Resale
Living Area
2,377 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
BaseboardRadiator
Heat Fuel
Oil
Cooling
None
Fireplaces
3
Laundry
Main Level
Laundry Location
Formally the old Buttery
Appliances
Gas CooktopOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
Crawl SpaceFull
In-Law Apartment
PossibleOver Garage
Additional Rooms
Sitting RoomSolarium

Exterior & Lot

Lot Size
4.53 acres
Zoning
RR
Garage / Parking
2 garage spaces5 total parking spacesBarnDetached GarageOff Street Parking
Waterfront
Direct waterfront
Waterfront Details
PondBrook
Water Source
Private Well
Sewer
Septic
Flood Zone
Yes
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
TerraceFruit TreesBarnGuttersGarden AreaStone WallPatio
Lot Description
TreedProfessionally LandscapedRolling

Listing & Financials

Property Taxes
$8,211 / Annually
Days on Market
265
MLS #
24136619
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jane Hinkel

(860) 459-0718

William Pitt Sotheby's Int'l

(860) 567-0806

Co-Listed By

Phil Fox

William Pitt Sotheby's Int'l

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 6:01 AM UTC.